14) Obtain the major product for 1,2- and 1,4-addition reactions (a and b) of conjugated system first and then illustrate the mechanism via resonance-stabilized allyl carbocations. Also, achieve the major product for the addition reactions (e and d). Mechanism for both product formation via resonance-stabilized ally carbocations 1,4-addition Product (a) HBr 50°C 1,2-addition Product HBr -70°C (b) 1.4-addition Product 1,2-addition Product H-CI 70°C H-Br -60°C (d) (c) 15) For all Diels-Alder ([4+2] cycloaddition) reactions, provide the major product with proper regioselectivity (1,2-/1,3-/1.4-product) and stereoselectivity (meso/enantiomer and exo/lendo) preference. Show arrow pushing for all [4+2] cycloadditions. CO2ME heat Meso

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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Chapter10: Alcohols
Section: Chapter Questions
Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...
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14) Obtain the major product for 1,2- and 1,4-addition reactions (a and b) of conjugated system first and then
illustrate the mechanism via resonance-stabilized allyl carbocations. Also, achieve the major product for
the addition reactions (e and d).
1,4-addition Product
Mechanism for both product formation via resonance-stabilized
ally carbocations
(a)
HBr
50°C
1,2-addition Product
HBr
-70°C
(b)
1,4-addition Product
1,2-addition Product
H-CI
70°C
H-Br
-60°C
(c)
(d)
15) For all Diels-Alder ([4+2] cycloaddition) reactions, provide the major product with proper
regioselectivity (1,2-/1,3-/1,4-product) and stereoselectivity (meso/enantiomer and exo/endo)
preference. Show arrow pushing for all [4+2] cycloadditions.
heat
Meso
CO, Me
heat
Meso
CN
heat
Racemic
CN
COET
heat
Racemic
ČOEE
Transcribed Image Text:14) Obtain the major product for 1,2- and 1,4-addition reactions (a and b) of conjugated system first and then illustrate the mechanism via resonance-stabilized allyl carbocations. Also, achieve the major product for the addition reactions (e and d). 1,4-addition Product Mechanism for both product formation via resonance-stabilized ally carbocations (a) HBr 50°C 1,2-addition Product HBr -70°C (b) 1,4-addition Product 1,2-addition Product H-CI 70°C H-Br -60°C (c) (d) 15) For all Diels-Alder ([4+2] cycloaddition) reactions, provide the major product with proper regioselectivity (1,2-/1,3-/1,4-product) and stereoselectivity (meso/enantiomer and exo/endo) preference. Show arrow pushing for all [4+2] cycloadditions. heat Meso CO, Me heat Meso CN heat Racemic CN COET heat Racemic ČOEE
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